The Art of Asking

How To Make an Ask of Those Around You

A long time ago, Amanda Palmer did an incredible TED talk on the “Art of Asking.” The whole time I thought about how relevant her experience in music has been to my career in startups.

In her talk, Amanda spoke of how she often asks fans for money—and how another artist she had met refused to, because he was too embarrassed.

It reminded me how difficult making an ask is, and how too many entrepreneurs either don’t ask enough, or make asks in the wrong way.

Making Asks is a Good Thing:

Asks come in many ways. There are:

· Asks for intro’s

· Asks for advice

· Asks for money

And so on…

And every great entrepreneur makes asks. Making an ask doesn’t make founders weaker or look vulnerable. It makes founders look resourceful.

When entrepreneurs I’m invested in or advising ask me for something I’m glad they’ve told me what they need. If they haven’t asked for something in a long time, I wonder if they are trying to take everything on all by themselves, or if they don’t see all the obstacles in their path yet.

I look up to all the entrepreneurs we work with—it’s the reason we work with them. If they ask me for something that does not change my perception of their aptitude one bit.

In fact, not making asks sometimes makes founders look naïve.

Reasons Why People Don’t Make Asks:

They are afraid of Losing their Reputation:

Often—the greatest and most talented entrepreneurs are the ones who have the hardest time asking for help.

Why is that?

It’s because these are entrepreneurs who are used to being looked up to. They are used to giving, and helping, and have earned a reputation as “someone who knows what they are talking about.” Making an ask is sometimes an embarrassing thing. It says “I am not sure I can do this on my own, can you please assist me?” It’s an admittance that the entrepreneur, in fact, doesn’t know everything.

And that’s okay! No one knows everything, but it’s a hard ego-trip to leap over.

Relationship Dynamics:

When great entrepreneurs first engage with others, it’s usually a one-sided relationship. It’s a giving relationship. When I meet with brand new entrepreneurs I often am introducing them to others, giving them advice, helping them navigate new processes. I’m not initially receiving much in return.

But over time, as those entrepreneurs evolve, I’ve realized they have quite a bit to offer themselves. In fact, the skill sets of these people I give advice to often fills gaps in my own skill set.

But changing that social dynamic between us feels awkward and consists of lots of friction. I have to let this advisee in to my life—someone who has always felt like I’ve got everything under control, and admit I have a flaw, or am missing a point of expertise.

I’m sure many other advisors and investors have felt the same way.

The investors who originally backed Jeff Bezos and Larry Page/Sergey Brin originally were giving advice, and now likely receive advice in exchange. (This happens at a smaller scale too).

How Not to Make Asks:

On the flip side—some people make too many asks, or difficult asks. The sign of an unqualified entrepreneur is one who is constantly asking for large, difficult or vague things, without any hope of returning the favor. These are people who forget to be givers, and are constantly taking.

They ask, ask, ask and eventually exhaust their relationships. Both Guy Kawasaki and Gary V talk about how important it is to give, give, give and then take.

My opinion is that sometimes it’s okay to take first, as long as the ultimate intention of ultimately giving back is clear.

Everyone has something to give. On my very first day in startups the thing I had to give was a piece of my company, and free labor. I gave small pieces of equity in my first startup to people who were helping out, and was willing to run errands for people who asked, make intro’s if possible, and put together small projects at no charge.

After gaining experience, I was able to offer more and more, and now by the end of each conversation I have with someone new, I can typically think of at least some way to be helpful.

Start a Mutually Giving Relationship from Day One:

The best way to avoid future friction is by establishing a two-way relationship from the very beginning. If I talk with someone who has less startup experience than me, I can still find a way they can help me. Even if it’s in a really, really small way. It’s not because I’m selfish or trying to capitalize off of all my relationships. It’s because it has opened a door that swings both ways. It creates a deeper and richer relationship.

They know that they of course can ask me for things because I offer—and because they’ve approached me and I take the meeting.

When talking to someone with more experience than me, I end every conversation with: “How can I help you?”

There is nothing better than helping someone you look up to.

Make Asks—People Want to Help:

As hard as it is to believe—those around you, especially friends, really do want to help. Other entrepreneurs remember how hard starting a company was, peers appreciate the boat you’re in, and everyone realizes that going it alone is next to impossible.

When making an ask, ask for specific things. Show why it’s important for the company, and make sure the ask makes sense for the person you are speaking with.

Don’t let the asks be vague. Don’t ask “can you intro me to an investor?”

Rather rephrase and say:

“I see that you know these 5 people via Linkedin. They are all investing in the space I’m in, and I was wondering if you could intro me to 2 of them.”

That takes the burden off the person helping you, and will yield greater results.

If I Can Ever be Helpful to You, Please Let me Know:

And it would be crazy if I wrote this post and didn’t offer to help you if possible. So my email is ali@coventure.us